Dr. Chiles’ signature keynote address is entitled “What Now? What Next? What If” has been enormously successful at many scheduled speaking events. This is an outline of that address:

What Now?

(The Immediate, Grounding Phase)

Your job is a chapter, not the whole book. Right now, it’s about breathing, gathering facts, and starting small.

Sub-Point 1: Acknowledge Your Feelings (Without Judgment)

Info: It’s okay to feel shocked, sad, or even angry. These feelings are normal reactions, not weakness. At 50+, you’ve lived through many seasons—this is just another wave. Don’t shame yourself for grieving the idea of stability. Grief isn’t linear; it might surface as quiet sadness (“I miss my routine”) or sharp frustration (“This feels like a mistake”). Key insight: Your worth never tied to this job. You’ve carried decades of experience—this loss is about a role, not your value.

Exercise: Emotion Journaling (5 mins): Write one feeling (e.g., “I feel like I’m falling”). Then add: “This is temporary. My worth isn’t defined by this job.” Read it aloud while sipping tea. Why? Naming feelings reduces their power. For 50+: Add a line: “This feels big because my life has changed too—kids left, empty nest, new rhythms. This is one part.”

Sub-Point 2: Gather Your “What You Bring” List (Not Just the Job)

Info: Forgotten transferable skills? Think: “I organized complex projects,” “I listened patiently to frustrated clients,” “I managed budgets.” These are gold for any new field. Key insight: At 50+, you’ve mastered adaptive leadership—not just tasks. Your ability to navigate ambiguity (e.g., handling a client’s surprise request) is priceless in healthcare, education, or tech support roles where flexibility matters.

Exercise: Skills Radar (10 mins): On paper, draw a circle with your job title at center. List 3 skills you used daily (e.g., “Problem-solving,” “Team Communication”). Now, add a new context: “This skill helped me fix a client’s software issue last week.” For 50+: Include why it matters now: “My budgeting skill helped my granddaughter manage her savings account—now I see how this could help others.”

Sub-Point 3: Resume Rewrite (The “What Now?” Action)

Info: Your resume shouldn’t say “looking for job” — that screams desperation. Instead, frame it as growth. Example: Change “Teacher” → “Learning Strategist” or “Customer Experience Specialist.” Key insight: Employers see your experience as a strength, not a gap. A 50+ career is built on trust; your resume should reflect that.

Exercise: Resume Rewrite (7 mins): Take one job title (“Senior Analyst”) and rewrite it as: “Analyst who turned data into clear client action plans—like helping my daughter budget for college.” For 50+: Add a line: “This role uses my experience to make complex things simple, like I did with my late husband’s medical bills.”

Sub-Point 4: Outreach (The “What Now?” Connection)

Info: Cold emails fail. For 50+, ask someone in your network—not just LinkedIn. Example: “Hi Maria, you’ve been in X field for 30 years! I’m exploring new paths and would love to hear how you’d handle [specific task].” Key insight: Your network is still valuable—even if unused. A 2019 AARP study found 78% of seniors over 65 have still relevant skills for emerging fields (e.g., healthcare tech).

Exercise: Outreach Script (5 mins): Draft a 3-sentence message to a colleague: “I’m exploring new opportunities and would value your perspective. Could I grab coffee next week?” For 50+: Add: “If they say no, I’ll just say ‘Thanks for the chat!’—no pressure.”

Sub-Point 5: Tiny Action (The “What Now?” Habit)

Info: Starting small builds momentum. Key insight: At 50+, you don’t need to “figure it all out.” Your superpower is consistency, not speed. A 10-minute daily action (e.g., researching one role) beats a 3-hour panic session.

Exercise: Tiny Action (2 mins): Write down one thing you’ll do tomorrow (e.g., “Call my cousin about X field”). Say it out loud while brushing teeth. For 50+: Add: “This is tiny because I’ve done tiny things for decades—like watering plants.”

What Next?

(The Transition Planning)
You’re not starting over. You’re stepping into a new season of your story.

    Sub-Point 1: Explore Fields That Use Your Skills

    Info: “Switching fields” isn’t failure—it’s leveraging experience. Example: A retired engineer’s “problem-solving” is now “AI ethics consultant.” Key insight: Your 50+ career built resilience—not just skills. You’ve adapted to change your whole life; this is the next step.

    Exercise: Field Research (10 mins): List 3 jobs where you’d use “listening” or “budgeting.” Example: “Healthcare coordinator” uses listening for patient needs; “Financial planner” uses budgeting for clients. For 50+: Add: “I’ll start with what I love—like helping people feel heard.”

    Sub-Point 2: New Educational Skills (Not “Learn Everything”)

    Info: You don’t need a degree to learn new tools. Example: A 62-year-old teacher uses free Coursera courses on digital literacy—not for tech, but to understand how her students use phones to research health info. Key insight: Your brain is wired for learning; the barrier is time/energy.

    Exercise: Skill Audit (5 mins): Write down one skill you want to learn (e.g., “using a new CRM”). Then add: “I’ll take 20 minutes/day to watch a YouTube tutorial.” For 50+: Add: “This isn’t about being ‘behind’—it’s about staying curious.”

    Sub-Point 3: Career Transition (The “What Next?” Path)

    Info: Don’t chase the “perfect” job. Example: A 58-year-old accountant took a part-time role as caregiver—using her budgeting to track expenses for clients. Key insight: Your transition might look like adding a new skill (e.g., caregiving) rather than replacing it.

    Exercise: Transition Map (7 mins): Draw a simple path: “My current skills → New role → How I’ll use my old skills.” Example: “Budgeting → Track client expenses → Help them feel secure.” For 50+: Add: “This is like adding a new chapter to my book—my story continues.”

    Sub-Point 4: Job Search (The “What Next?” Strategy)

    Info: Avoid generic applications. Target companies that value experience: e.g., A local hospital hires 50+ for patient coordinator—they need your calm under pressure. Key insight: Your age is a benefit, not a barrier. 65% of hiring managers say “experience” matters more than youth (LinkedIn, 2023).

    Exercise: Targeted Application (10 mins): Find one job description with “experience valued.” Write: “My 30 years in X field helped me [specific outcome].” For 50+: Add: “This isn’t a resume—it’s proof I’m ready for this new chapter.”

    Sub-Point 5: Support System (The “What Next?” Safety Net)

    Info: Isolation is the biggest risk. Your support system might be yourself—like writing down: “I’m okay with uncertainty.” Key insight: At 50+, you’ve navigated loss; now you need to navigate this.

    Exercise: Support Note (2 mins): Text a friend: “Thinking of you—thoughts on my new path?” If no reply, say: “No worries—I’ll call tomorrow.” For 50+: Add: “This is like tending a garden: I plant seeds, water them, and wait.”

    What If?

    (The “What If?” Scenarios)
    Your new life isn’t defined by the job loss—it’s shaped by how you choose to see it.

      Sub-Point 1: Changing Fields?

      Info: Switching fields (e.g., from teaching to healthcare) is not “starting over.” It’s using your experience as a foundation. Example: A 64-year-old teacher became a senior care aide—using her classroom management skills to keep patients calm. Key insight: Your past self would be proud you’re building on that legacy, not replacing it.

      Exercise: “If I switched fields, which old skill helps me?” Write the answer (e.g., “Listening”). Say it aloud: “My listening makes me a better caregiver.”

      Sub-Point 2: Seeking New Education?

      Info: A 50+ course isn’t about “catching up”—it’s about curiosity. Example: A 61-year-old accountant took a free “financial wellness” course to understand her clients’ needs. Key insight: You’re not learning for a job—you’re learning to feel less alone in the transition.

      Exercise: “What one thing would make me curious?” (e.g., “How do I talk to my doctor about chronic pain?”). Watch 1 video on it. For 50+: Add: “This isn’t a test—it’s a conversation with myself.”

      Sub-Point 3: Trying Something Entirely Different?

      Info: “Entirely different” = honoring your curiosity. Example: A 57-year-old engineer started urban farming—using her project management to grow herbs. Key insight: Your age isn’t a limit; it’s a reason you’re wise enough for this.

      Exercise: “What’s one small, joyful thing I could try?” (e.g., “Planting one seed”). Do it today. For 50+: Add: “This is like my first garden—no pressure to harvest.”

      Sub-Point 4: Field Switch Feeling ‘Too Simple’?

      Info: “Simple” isn’t boring—it’s freedom. Example: A 63-year-old teacher became a community gardener—she solves problems with her hands, not spreadsheets. Key insight: Your old role had “rules”; this has joy.

      Exercise: “What would make this feel meaningful?” Write: “Helping others grow.” Say it: “I’m growing joy, too.”

      Sub-Point 5: ‘What If I Fail?’

      Info: Failure isn’t a dead end. Example: A 60-year-old tried yoga—but it didn’t work. She said: “That’s okay. Now I’ll try walking.” Key insight: Your 50+ brain knows progress, not perfection.

      Exercise: “If this doesn’t work, what’s the smallest next step?” (e.g., “Walk to the mailbox”). Do it now. For 50+: Add: “This is like my first knitting project—no finished piece needed.”